


Dirty Work

by writingfiction



Category: Shameless (US)
Genre: Alternate Universe - 1920s, Angst, F/M, Flappers, Gen, Implied Sexual Content, Lots of confusion, M/M, Mobsters, Past Sexual Abuse, Prohibition, Roaring Twenties, Secret Identity, Secret Relationship, Sexual Tension
Language: English
Status: In-Progress
Published: 2018-01-03
Updated: 2018-01-03
Packaged: 2019-02-27 20:31:13
Rating: Mature
Warnings: Graphic Depictions Of Violence, Underage
Chapters: 3
Words: 3,857
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13256052
Author URL: https://archiveofourown.org/users/writingfiction/pseuds/writingfiction
Summary: “in the slums of Chicago, all bets are off”Secrets and drama follow the Shameless gang as men and women of the Roaring Twenties.





	1. a good fella

**Author's Note:**

> I wrote this between a few plan trips i’ve taken in the past few months and still don’t have any idea or direction for it. oh well

Phillip Gallagher was in shambles. All he ever wanted was to be in a committed, loving relationship and now that had abruptly ended with his ex-lover, Karen. He had watched her give birth to a child who was not his, and he had bled and cried for this child unbeknownst of his genetics. For leading him on this whole time, he had to give her props, but she had left him broken and saddened. Empty. So, he sat, at the Alibi Bar—a speakeasy where no one asked your name—and requested of the dark-skinned wife of the barkeep, Kevin Ball, for a vodka, dirty, and to keep them coming until he wasn’t coherent. Phillip was not a well-received man around Chicago, for despite being well-educated, he had gotten himself into some dirty business over the years. At the age of twenty-eight, his name was still on some blacklists around the state. But, in the slums of Chicago, all bets were off.

There he sat, at the bar, a hand in his dirty-blonde curls that deemed him juvenile and unruly—exactly what he was. His black slacks wrinkled, along with a white buttoned top in the same state. He had a black suit jacket, but it was discarded on the floor of the bar.

“So, Phillip, what’s a striking young man like yourself doing here at this hour?” Kevin asked, his jokes good-natured as he poured Phillip another drink.

Phillip just groaned and scrubbed his face in agony. Kevin laughed heartily, before flashing a smile. “I’m assuming from your state it has something to do with your Missus?”

“More like the lack thereof,” Phillip muttered, causing Kevin to nod sympathetically. “Drinks are free for the rest of the night, my friend. Need to calm those bitches,” Kevin smirked, and Phillip smiled at his friend’s crass behavior.

“I’ll drink to that,” Phillip said, chuckling before taking a swallow of the alcohol.

Kevin leaned forward, rubbing his goateed chin. “Lip, I have’ta ask you something that I’m a bit unsure of.” The man in question smiled at the use of the nickname, before nodding for his good friend to continue.

“I’d like to hire a few flapper girls to really get this place movin’— we got an offer, do you think we should take it and go forward?”

Lip smiled, a bit crude in the fact, before nodding. “A few flapper girls...and they’d wear the bits and pieces like they do back in Manhattan?”

Kevin nodded, mind going into overdrive. “Well, of course!” Lip smiled and filled his glass. “Well, I suppose I’ll drink to that.”

———

About three weeks time, Lip returned to the Alibi Bar, to see the place turned on it’s head. He walked into the small building, being hit by a smoky haze. This was not unfamiliar to the young man, who smoked both cigarettes and cigars rather often. He entered into the establishment to see a crowd of men, sitting at the bar, or seated at tables, but one thing was different; the women.

The young flapper ladies sitting on tables, chairs and the like, laughing loudly, smoking their own cigarettes, or getting cozy with a few of the residents. Lip smiled. Kevin had gone through with the offer.

Lip approached the bar, and Veronica, Kevin’s wife, noticed him. “Phillip! It’s so good to see you,” she smiled widely, causing Lip to nod, smile and sit in front of her. “Glad to know I’m still missed in some parts,” the young man stated, as he took his suit jacket and fedora hat off his head. Veronica tsked at his tone, before pouring him a Scotch. “Your sister misses you somethin’ awful,” Veronica said, as Lip took a drawn-out sip of his drink. “If she missed me that bad she’d call,” he said, voice quick and curt.

The woman scoffed before looking at the boy. “Once you get your head on straight, you’d betta’ get down to that ramshackle house and save face,” Veronica said, and Lip shrugged but stayed quiet, knowing not to talk poorly towards Veronica Fisher. She was small, but did she have spite.

“Lip, look out. Fox on the loose, heading your way,” Kevin warned, as he cleaned a glass. Lip tossed a glance over his shoulder to see a slender woman, with a fringed black dress and sheer gloves making her way to him.

She sat next to him, not sparing him a second glance. “Cherry vodka, on the rocks,” the woman spoke, silky and seductive, with a hint of an accent that Lip couldn’t place.

Her eyes were painted with more charcoal then Lip usually saw on flapper girls, but it suited her. It made her obsidian eyes piercing and exquisite. She had pulled Lip into a trance.

She sipped her poison slowly, her wine-red lips leaving stains on the glass. She then turned to Lip, and through narrowed eyes, glanced his way.

“Mind if I bum a smoke from ya?” She asked, her voice raspier then Lip imagined. He nodded, grabbing the light and Camels from his jacket pocket. As she inserted the nicotine into her mouth, he lit it and tried not to stare.

He pulled away and she took the cigarette from her mouth, before blowing the smoke to the side. “So, what’s a girl gotta do to get some time with a fella like you?” She asked, her voice innocent, but Lip could see her sultry act behind the cigarette dangling from her gloved fingertips.

Lip smiled. “Little lady, all you gotta do was ask,” he smirked, and her face hardly changed expression. She was harder to break, he realized. Many women would be melting at his feet by that time.

“You seem like trouble,” she said, vaguely, as the blew another cloud of smoke into the air. Lip noticed that her hair was cut in the front, a style he had never seen before, especially on flappers. It was tucked up into a bob in the back, making him wonder what it all looked like, hanging free.

“You seem worse,” he replied, and she smirked, putting out her cigarette in the nearby ashtray. “Oh,” she whispered. “I am.”

With that, she walked away, her black boa hanging loosely from both arms, to where it dipped right over her rear end. Lip was watching her strut away, when Kevin stole him from his trance.

“She was our first applicant. V’s the only one who knows her real name, but her surname’s Milkovich.”

“Sounds Russian,” Lip supplied, before lighting up his own smoke and inhaling deeply.

“That’s what I was thinking,” Kevin replied, making Lip nod and study the girl. She was sitting atop a stool, teasing a man by pulling him forward by his tie, and whispering something while the cigarette dangled from those deadly lips.

“I need to know more,” Lip said, almost pleading, as Kevin put up his hands in defense. “Talk to the wife,” he said, motioning to the lady in question, who was shooting down offers of sexual favors with vigor.

“Veronica—who’s that girl?” Lip asked suddenly, making Veronica look up. “Name’s Milkovich. Doesn’t like havin’ her first name out. Does a helluva job, though.”

Lip nodded, before grabbing his coat and placing his fedora hat atop his head. “Thanks for the drinks, boys,” Lip said, before placing a bill on the countertop. “I got some people to see.”


	2. family matters

**Summary for the Chapter:**

> Lip goes back home

Lip approached home with a weary demeanor. The home was falling apart at the seams, and for all he knew his older sister had been trying to keep it up, on her own.

He walked up the sodden steps to see his younger brother Carl, sitting inside, listening to the radio. Lip knocked on the door, causing the boy inside to do nothing but yell for Fiona.

As no one came to the door, he decided to walk in. It was his house, too.

“Hey, kiddo,” Lip greeted easily, making Carl jump up and smile. “Lip! You’re home!” This caused a chaotic break to ensure throughout the home. Debbie and Liam ran downstairs, as did Ian, all exclaiming that their eldest brother was home. After bear hugs were distributed, Lip leaned against the wall, lighting a cigarette. “Fi home?”

Debbie pursed her lips. “Why?”

“Gotta ask her some questions, Debs, thas’ all,” he said, the cigarette causing his words to slur and stick together as he spoke.

The redhead nodded, before running about the house, yelling this and that for Fiona.

“Hey, quit your hollerin’, I’m comin’!” She yelled, from the top of the steps, before clomping down them gracefully. When she registered who was there, a smile broke out on her tired and dirty face.

“Jesus, if I had known it was you causin’ all this ruckus, I woulda came to join ya,” Fiona said happily, as she tightly hugged her brother. He half-heartedly returned the favor. “We gotta talk, Fi.”

She nodded, numbly grabbing the boy’s hand and pulling him into the kitchen. “What do you need? I can’t give you money, Lip,” she sighed, taking the burning cigarette from Lip’s hand, before taking a long drag.

“I don’t need your money, Fi. I’m doin’ fine,” Lip mumbled, before sighing. “You know any Milkovich’s from ‘round here?”

Fiona shook her head. “Never heard that name. Someone after you?”

“Nah, more like me after him,” Lip said, and Fiona shrugged, taking another drag. “Never heard of ‘em,” she mumbled, smoke tumbling from her mouth as she spoke.

Lip rolled his eyes and turned on a worn-out heel, when pale, slender fingers grabbed his black-clothed bicep.

“Lip, wait. Why don’t you stay?” Fiona whispered, and he saw the fear in his oldest sister’s eyes, her bottom lip trembling as she continued. “Jimmy left me, Lip. He left for some exotic broad, and I don’t know what to do,” she whispered, and Lip sighed. “I told you not to get involved with him, Fi,” he recited, not feeling half as much sympathy as he knew he should, even when he saw a small tear glisten as it fell down her cheek.

She just wiped her tired eyes. “No use in cryin’ any longer. He’s not comin’ ‘round again.”

Lip nodded. “Why’do ya wanna find this Milkovich, again?”  
“Just business,” Lip answered ominously. Fiona rubbed her temples, before wrapping her hair up in a du-rag. “You’d better not be getting into that mobster shit again. That nearly got you killed,” she hissed, and he rolled his eyes.

“I’m fine, Fi, Christ,” Lip snarled, the feeling in the room growing cold again.

Ian walked in, and backtracked when he saw that the two were basically at the other’s neck. Fiona turned and focused on him. “Where are you headed?” She asked, voice tight as she glared at the ginger.

“Out,” he muttered, as he threw on a black sport coat before brushing past his older siblings.

The twenty-nine year old threw her hands up in aggravation. “You’re all impossible! I break my back for y’all and all I get is a slap in the face!” She cried, and Lip drew his mouth into a thin line. “Sorry for comin’ back, sis,” he whispered, voice thick from anger. “Don’t expect to see me anytime soon.”

She just raked her fingers through her stringy brown hair, on the edge of a breakdown as Lip went back to the parlor.

Debbie and Carl looked at him, moon-eyed in the face. “Lip, aren’t you stayin’ here?” Carl asked, his teenage bravado shot down as the thought of someone else leaving scared him.

“I’ll be back soon,” he mustered up a blank face, before slipping his fedora on and lighting yet another cigarette. “Don’t give Fi any more trouble, now,” he mumbled before stepping into the night.

———

Ian hated walking around Chicago at night.

The place was unnerving in itself, but at night it seemed that all the monsters came out to play. The men and women of the sewers, Ian’s father had called them. Funnily enough, that’s where he lay now, for all Ian knew. He pulled the sport coat tighter, trying not to shiver as the winter wind blew in.

He walked up the street, before tossing a glance across the way to a burning streetlight.

He felt a tap on his shoulder, and turned out of surprise. “Calm down, boy,” a rough voice said, and Ian did once he realized who it was. Crooked smile, jet-black hair, translucent skin. Mickey.

“Hi, Mick,” he smiled nervously. “Let’s get out of the light,” the vampiric boy said, whisking the ginger out of sight. This was a common occurrence, the two meeting up and, well...doing unspeakable things that absolutely no one could’ve known about.

Mostly for Mickey’s sake.

Ian didn’t have a reputation to ruin, but Mickey had everything to lose. His father was involved with the Russian mafia, and was extremely intolerant of basically everything when it came to his son. So Mickey’s secret love affair had to be tucked and pinned safely under wraps. He knew that if Terry Milkovich found out about his secret, he and Ian would be dead by morning.

So, they met every Saturday night, at different places, meeting for about an hour or two. Outside of these rendezvous, they did not acknowledge one another, so they wouldn’t compromise the other. It was hard, especially for Ian, who had soon after meeting Mickey fallen head-over-heels in love.

After their meeting, Ian stood by the streetlight, smoking a cigarette, and Mickey asked for a drag. As he puffed, he looked over at Ian.

“So, my sister’s workin’ at that Alibi speakeasy. Look out for her?”

Mickey had always held a soft spot for Mandy, his sister, who had been violently exposed to the sexual natures of life much too early. Ian knew of the girl, and Mickey knew that he was harmless to her. Ian smiled at the mention. “‘Course, Mick.”

“Don’t call me that, kitten,” he replied, taking another long drag of the nicotine, before dropping it on the ground and crushing it under his leather loafer.

Ian tried not to stare too fondly as the boy disappeared into the dark, dark night.


	3. only when the clock strikes twelve

**Summary for the Chapter:**

> Lip meets up with Mandy, and this time their interaction is more carnal then before. THIS CHAPTER IS BASICALLY SMUT BUT NOTHING TOO DETAILED

Lip Gallagher went back the Alibi speakeasy that following evening. In fact, as he walked in, he was bubbling over with anxiety. As he walked in, this time the noxious smoke did nothing to phase him. He walked in, trying too hard to act casual, and approached the bar. “Hey, Kev,” he mumbled a greeting to the barkeep. “Gimme a double,” he requested, slapping a few dollar bills on the table.

“Jesus, Lip, you keep getting dragged through the mud? Whenever you’ve come in lately, you’ve looked like hell,” a man at the bar said, and Lip threw a sidelong glance his way. “Stay outta my business, Tommy.”

Kevin sat the drink in front of Lip, before nudging the boy. “Our fox from your last visit keeps giving you eyes,” he chuckled, and Lip perked up instantly.

His blue eyes looked around in curiosity, before glancing behind him to see her, sitting across the room. He turned back to Kev, and swallowed hard. “She’s stuck on me, Kev,” he admitted, and Kevin laughed. “Go give ‘er some entertainment. Go, go!”

Lip anxiously stood, before taking a deep breath, lighting a cigarette, and slowly sauntering toward her. She looked up at him, her dark eyes hooded as she showed the ghost of a smile.

“Need a light?” he asked, noticing the unlit Camel in her gloved hand. “Thank you,” she replied, before sticking the cig in her mouth as he pulled a matchbox from his pocket and quickly drew a flame.

Once she exhaled a cloud of smoke from her mouth, he couldn’t help but think how effortless she made the small smoke rings look as she created them.

“Baby, you’ve got some talent,” he complimented, and her cheeks flushed a deep pink. God, she was precious.

“That’s not the only thing I can do,” she started, her lipstick flawlessly grasping the stick in her mouth, while tucking a loose curl behind her plumed headband.

“Well, sweetheart, indulge me,” Lip said, leaning against the back of the chair, taking a drag. “Well, my favorite thing,” she said, peering at him through her eyelashes, “has to be getting to know a fella who specializes in makin’ a girl like me...feel like a million bucks,” she smirked, and he chuckled, not taking the cigarette from his mouth. “Babydoll, what do you mean?” He inquired flirtatiously, knowing exactly what she meant.

“Oh,” her voice got husky. “I think you know exactly what I mean,” she whispered, glancing down at his plush lips, then back up to his icey blue eyes.

She leaned forward, not so close to Lip that he could feel her breath but close enough that he could feel their building tension. She wrapped a covered hand around his loose black tie, yanking it slightly, while making him stifle a groan. “Didn’t your momma ever tell you to keep your tie straight, mister?” she played innocent, but smirking as she crawled closer to him, her fingers brushing against the nape of his neck and up his jaw. Her dark brown eyes were bearing holes into his own blue ones.

Lip recognized the intensity she was harboring. The need, to connect with someone, the want for it to be dirty, rough, raunchy—anything and everything any mother would never approve of. He could see that she wanted him to take her, right there, in the dirtiest way possible, and by God, he wanted the same thing. He wanted to feel her, intimately and otherwise—she was irresistible.

“Let’s take this upstairs?” She pondered, her pouty lips waiting for his answer. He hardly hesitated. “Lead the way, dollface.” His suave demeanor make him seem untouchable, as did her own demeanor, but the two of them were both bursting at the seams once she took him behind a closed, locked door, the need for intimacy flowing through their veins.

“I want you to take me,” she whispered, breathlessly, as she pulled him close, with use of the thin fabric around his neck, and he bit his lip. “Babydoll, I know,” he chuckled, as she stared at him. She wanted this, oh, yes she did, but she didn’t know what to do next. Now she had him, but what now?

“C’mere,” he whispered, before tipping her chin up as his lips met hers, making her kiss him with a fever that was only unleashed the moment his hands found her waist, clutched her tight, and brushed his tongue against her bottom lip. They deepened the kiss, before he broke away. Looking dumbstruck, Lip panted as he looked at her. He traced her jaw, a slight smirk on his face before she saw a fire in his eyes.

Something carnal, something deep, and something dark was coming up to the surface.

He gently took hold of her bicep, and looked at her. “I am not like any other man you have served under. When you say you want me to take you, I will do just that.”

But she just smirked, this time revealing her pearly teeth. “Darling,” she purred. “I knew that from the beginning. And, I’ve been waiting. Unleash it all,” she urged, as she unbuttoned his top collar.

She was worth more then a million bucks, Lip decided to himself in that moment. She was priceless.

He shoved her against the wall, making her gasp quickly, before kissing her passionately. They became a mess of mouths as she moaned softly, egging him on to kiss and nip at her pale neck. She tore the feathered headpiece from her scalp, making her long black hair tumble to her shoulders and Lip stared in awe. As he raked his large hands through her silky strands, he kissed her again. “You are extraordinary,” he mumbled against her lips. She just moaned in response, and he began kissing down her neck again, and once he got to the neckline of her low-cut dress, he chuckled.

“Babydoll, you gotta get out of this.”

She nodded happily, and then began to strip herself of all clothing. Her gloves, kitten heels and dress came off, and as she was reaching for her brassiere and pantyhose stockings, he grasped her hand.

“Wait a minute,” he whispered, holding her pinned against the wall. “Holy hell, baby—you...look like a million bucks,” he whispered, and this caused a pink heat of blush to flush up through her skin. “Oh, you’re just bein’ polite,” she whispered, as he gently tilted her chin up to meet his eyes.

“You are beautiful,” he confirmed, before leaning in to kiss her again, but this time it was different. Gentle, almost, sweet and loving, before she kissed back. When she kissed him back, she threw her arms around his neck, pulling him close to her so he could press his body against hers.

She broke the kiss, smirking as she rested her forehead on his, her nimble hands going in for his now-loose tie, shucking it from his neck, and beginning to unbutton the rest of his shirt. He groaned when her cold hands reached his tan chest, and when her fingers traced his hard muscles, his hands grabbed her and rocked their bodies together. When that contact was made, she could feel his hardness against her thigh, making her blush feverishly and heart beat a skip or two.

He finally broke away from her, and she went over to the bed, watching him hurriedly unbuckle his belt and slacks. When he was standing in nothing but his undergarments, he glanced at her, and she felt his darkness—the one she had seen earlier, in his eyes—and it excited her and terrified her all at once.

She beckoned him closer, and he collided with her, his exuberance electrifying.

As they connected, Lip felt strong. He felt in control, and this nameless beauty, this Milkovich beneath him was absolutely beautiful. Her pale skin, now decorated in bruises of pleasure, her black hair spread about in silky perfection, her soft moans that got higher with each one of his thrusts—absolute perfection. When he gripped her hips and pushed himself inside her, he felt alive.

She looked up at him, almost pleadingly. “God, I-I’m almost-“ she whimpered breathlessly, and Lip growled, while thrusting faster. “Come on, babydoll, let go,” he replied, urging to see her come undone. As she did, her lips shaped in a perfect circle as the waves of pleasure washed over her and she whined, meekly. As she came down from her high, he pulled out and she crawled forward. Reaching for his manhood, she began to pleasure him with those sinful lips of hers.

“Oh, oh, yes, babydoll—“ Lip groaned, placing his hands on the back of her neck and guiding her bobbing head. As he soon after reached orgasm, she looked up at him through her eyelashes, those obsidian eyes full of lust making Lip wonder: is she feeling what I am?


End file.
